CN1450999A - 新的哌嗪衍生物 - Google Patents
新的哌嗪衍生物 Download PDFInfo
- Publication number
- CN1450999A CN1450999A CN01807616A CN01807616A CN1450999A CN 1450999 A CN1450999 A CN 1450999A CN 01807616 A CN01807616 A CN 01807616A CN 01807616 A CN01807616 A CN 01807616A CN 1450999 A CN1450999 A CN 1450999A
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- CN
- China
- Prior art keywords
- base
- amino
- wan
- tang
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000004885 piperazines Chemical class 0.000 title description 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 233
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 239000002585 base Substances 0.000 claims description 1968
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 431
- -1 alkyl sulfide Chemical compound 0.000 claims description 315
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 141
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 130
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 81
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 70
- 239000011541 reaction mixture Substances 0.000 claims description 70
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 55
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 53
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 53
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 53
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 49
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 39
- 239000001301 oxygen Substances 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000001475 halogen functional group Chemical group 0.000 claims description 36
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- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 34
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- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 31
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- 238000000034 method Methods 0.000 claims description 28
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 21
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 17
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
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- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
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- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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DE60213958T2 (de) | 2001-02-27 | 2007-08-30 | Migenix Corp., San Diego | Aryl-n-cyanoguanidine derivate und deren verwendung |
CN1529699A (zh) * | 2001-06-20 | 2004-09-15 | �Ʒ� | 新的磺酸衍生物 |
US6812230B2 (en) * | 2001-08-07 | 2004-11-02 | Schering Aktiengesellschaft | Non-peptide CCR1 receptor antagonists for the treatment of progressive renal fibrosis |
US7655658B2 (en) | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
US7732451B2 (en) * | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
AU2002331064B2 (en) * | 2001-08-10 | 2007-08-23 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
US7354923B2 (en) * | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
US7456184B2 (en) | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
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AU2003202495B2 (en) * | 2002-01-11 | 2006-07-20 | Sankyo Company, Limited | Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these |
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CN101538254B (zh) * | 2003-12-23 | 2011-07-27 | 赛诺菲-安万特 | 1-哌嗪-和1-高哌嗪-羧酸酯衍生物、制备和其治疗用途 |
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